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C s ‐Symmetric Donor–Acceptor Bis(thiazole)s: Synthesis and Photophysical, Electrochemical, and Computational Studies
Author(s) -
Maragani Ramesh,
Bijesh S.,
Sharma Rekha,
Misra Rajneesh
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700274
Subject(s) - chemistry , thiazole , cycloaddition , electrochemistry , acceptor , electron donor , stereochemistry , photochemistry , computational chemistry , catalysis , organic chemistry , physics , electrode , condensed matter physics
We herein report the design and synthesis of C s ‐symmetric donor–acceptor (D–A) molecular systems that have electron‐donating and electron‐withdrawing groups of the type D‐π‐A‐π‐D and D‐A 1 ‐A‐A 1 ‐D by using a Pd‐catalyzed Sonogshira cross‐coupling and [2+2] cycloaddition–retroelectrocyclization reactions. The photophysical and electrochemical properties as well as computational studies of these systems were explored, and strong donor–acceptor interactions were found. The [2+2] cycloaddition–retroelectrocyclization reaction pathway was studied by computational calculations, which revealed that bis(thiazole)s that contain donor groups at the terminal positions were favored in the reaction with tetracyanoethene (TCNE), whereas bis(thiazole)s that contain electron‐withdrawing groups were disfavored.